This invention relates to novel N-(heterocyclicaminocarbonyl)indole sulfonamides which are useful as agricultural chemicals and, in particular, as herbicidal agents.
Canadian Pat. No. 747,920 (issued 12/6/66, Upjohn) discloses 3-(alkylcarbamoylsulfamoyl)-1-alkylindole-2-carboxylic acids and esters (i) as sedatives, diuretics, antifungal agents and/or sun screens ##STR1## where R and R.sub.2 are C.sub.1 -C.sub.4 alkyl, and
R.sub.1 is H or C.sub.1 -C.sub.4 alkyl. PA1 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Y is methyl or methoxy; or their agriculturally suitable salts; PA1 (a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA1 R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, Cl or Br; PA1 R.sub.4 is H, C.sub.1 -C.sub.4 alkyl, cyanoethyl, C.sub.5 -C.sub.6 cycloalkyl, benzyl, phenyl substituted with Cl or NO.sub.2, or C(O)R.sub.6 ; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, or NR.sub.7 R.sub.8 ; PA1 R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.9 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.11 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.10 is ##STR11## X is CH.sub.3 or OCH.sub.3 ; Y is H, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3, Cl, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3 or CF.sub.3 ; PA1 Y.sup.1 is H, CH.sub.3, OCH.sub.3, Cl or OCH.sub.2 CH.sub.3 ; and PA1 Z is CH, N, CCH.sub.3 CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl, CCl, CBr or CF; PA1 R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, CO.sub.2 R.sub.6, C(O)NR.sub.7 R.sub.8, C(O)R.sub.10, SO.sub.2 R.sub.10, or SO.sub.2 NR.sub.11 R.sub.12 ; PA1 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl or SO.sub.2 C.sub.6 H.sub.5 ; PA1 R.sub.3 is H, F, Cl, Br, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy or NO.sub.2 ; PA1 R.sub.4 is H, Cl or Br; PA1 R.sub.5 is H or CH.sub.3 ; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.7 and R.sub.8 are independently H or C.sub.1 -C.sub.4 alkyl, provided that the total number of carbon atoms is less than or equal to 4; PA1 R.sub.9 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.10 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.11 and R.sub.12 are independently C.sub.1 -C.sub.3 alkyl, provided that the total number of carbon atoms is less than or equal to 4. PA1 m is 0, 1 or 2; PA1 A is ##STR13## X is CH.sub.3 or OCH.sub.3 ; Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, Cl, H, C.sub.2 H.sub.5 or N(CH.sub.3).sub.2 ; and PA1 Z is CH or N; PA1 (1) when R.sub.2 is SO.sub.2 C.sub.6 H.sub.5, then R.sub.1 and R are H or C.sub.1 -C.sub.4 alkyl. PA1 (2) when Y is Cl, then Z is CH; and PA1 (3) when m is O, then R.sub.9 is C.sub.1 -C.sub.3 alkyl. PA1 (1) Compounds of the generic scope of Formula I where R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, CO.sub.2 R.sub.6, C(O)NR.sub.7 R.sup.8, SO.sub.2 NR.sub.11 R.sub.12 or SO.sub.2 R.sub.10 ; and R.sub.5 is H; PA1 (2) Compounds of Preferred (1) where R.sub.3 and R.sub.4 are H; PA1 (3) Compounds of Preferred (2) where R.sub.2 is H or CH.sub.3 ; PA1 (4) Compounds of Preferred (3) where R.sub.1 is H, CO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3 or SO.sub.2 N(CH.sub.3).sub.2 ; PA1 (5) Compounds of Preferred (4) where Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; PA1 (6) Compounds of the generic scope of Formula II where R is H, C.sub.1 -C.sub.3 alkyl, (CH.sub.2).sub.m CO.sub.2 R.sub.9, SO.sub.2 R.sub.10 or SO.sub.2 NR.sub.11 R.sub.12 ; and R.sub.5 is H; PA1 (7) Compounds of Preferred (6) where R.sub.3 and R.sub.4 are H; PA1 (8) Compounds of Preferred (7) where R.sub.2 is H or CH.sub.3 ; PA1 (9) Compounds of Preferred (8) where R is H, CH.sub.3 or (CH.sub.2).sub.m CO.sub.2 --(C.sub.1 -C.sub.3 alkyl); and PA1 (10) Compounds of Preferred (9) where Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl.
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula ##STR2## wherein R.sub.1 is ##STR3## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
provided that:
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful an antidiabetic agents: ##STR4## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR5## wherein R is butyl, phenyl or ##STR6## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR7## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR8## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974), ##STR9## wherein R is pyridyl.
U.S. patent application Ser. No. 244,172 discloses herbicidal compounds of formulae ##STR10## wherein R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, NO.sub.2, CN, C(O)CCl.sub.3, SO.sub.2 R.sub.11, C(O)R.sub.5 or CO.sub.2 H;
and their agriculturally suitable salts.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.